Round: 25 Ground: Clay
| ITF Tunisia F28 | 2016/10/17 08:30 | Dmitriev, Kirill v Derdoy, Felipe | 6-0,6-2 |
| ITF Tunisia F28 | 2016/10/16 08:30 | Dmitriev, Kirill v Bonapart, Casper | 2-6,6-2,6-4 |
| ITF Serbia F6 | 2016/09/06 08:30 | Gojo, Borna v Dmitriev, Kirill | 6-3,6-7,6-3 |
| ITF Austria F8 | 2016/08/31 10:05 | Dmitriev, Kirill v Nema, Patrik | 3-6,2-6 |
| ITF Serbia F2 | 2016/07/26 13:10 | Dmitriev, Kirill v Filipenko, Viktor | 6-2,2-6,4-6 |
| ITF Serbia F1 | 2016/07/21 08:00 | Nerman Fatic v Dmitriev, Kirill | 6-4,6-3 |
| ITF Serbia F1 | 2016/07/20 07:30 | Semjan, Marek v Dmitriev, Kirill | 3-6,2-6 |
| ITF Turkey F21 | 2016/05/26 07:30 | Choi, Seungri v Dmitriev, Kirill | 6-4,6-2 |
| ITF Tunisia F27 | 2016/10/12 12:40 | Marti, Javier v Monteiro, Joao | 6-2,6-4 |
| ITF Portugal F12 | 2016/10/05 09:15 | Lorenzo Giustino v Monteiro, Joao | 6-4,6-2 |
| ITF Portugal F11 | 2016/09/28 13:35 | Mertens, Yannick v Monteiro, Joao | 6-3,6-4 |
| ITF Spain F29 | 2016/09/08 10:55 | Romero de Avila Senise, Alberto v Monteiro, Joao | 6-1,6-4 |
| ITF Spain F29 | 2016/09/07 12:05 | Monteiro, Joao v Pla Malfeito, Jaume | 6-3,3-6,6-3 |
| ITF Spain F29 | 2016/09/05 12:15 | Morr, Jonathan v Monteiro, Joao | 4-6,1-6 |
| ITF Spain F27 | 2016/08/23 16:30 | Monteiro, Joao v Nicola Kuhn | 2-6,6-2,3-6 |
| ITF Spain F26 | 2016/08/19 15:40 | Monteiro, Joao v Brizzi, Alberto | 3-6,1-6 |